57786-49-9

Usage

Class of organic compounds

Benzamides

Use in pharmaceutical industry

Building block or intermediate in drug synthesis

Chemical structure

Benzene ring attached to an amide functional group and a pyridine ring

Applications

Development of potential drug candidates and medicinal chemistry research
Suitability for designing molecules with specific biological activities and therapeutic effects

InChI:InChI=1/C13H13N3O/c14-12-7-2-1-6-11(12)13(17)16-9-10-5-3-4-8-15-10/h1-8H,9,14H2,(H,16,17)

Upstream product

• 3731-51-9 2-(Aminomethyl)pyridine 
• 552-89-6 2-nitro-benzaldehyde 
• 118-48-9 isatoic anhydride 

Relevant academic research and scientific papers

UV-Light-Induced Dehydrogenative N -Acylation of Amines with 2-Nitrobenzaldehydes to Give 2-Aminobenzamides

A simple, mild, green, and efficient method for the synthesis of 2-aminobenzamides is highly desirable. Herein, we report the development of an efficient, one-pot strategy starting from 2-aminobenzaldehydes and amines with acetic acid in ethyl acetate/acetone using irradiation with UV light for the synthesis of 2-aminobenzamides in high yields; 32 examples proceeded successfully by this photo-induced protocol in up to 92% yield. The reaction was also readily achieved on a gram scale. The utility of the 2-aminobenzamide building block in organic synthesis was shown by their use in the preparation of quinazolinone derivatives. The method was applied to amino acid derivatives as the amine component, which smoothly gave N-(2-aminobenzoyl)acetate derivatives at room temperature. Finally, a plausible mechanism is proposed.

Synthesis, Evaluation and Proposed Binding Pose of Substituted Spiro-Oxindole Dihydroquinazolinones as IRAP Inhibitors

Insulin-regulated aminopeptidase (IRAP) is a new potential macromolecular target for drugs aimed for treatment of cognitive disorders. Inhibition of IRAP by angiotensin IV (Ang IV) improves the memory and learning in rats. The majority of the known IRAP inhibitors are peptidic in character and suffer from poor pharmacokinetic properties. Herein, we present a series of small non-peptide IRAP inhibitors derived from a spiro-oxindole dihydroquinazolinone screening hit (pIC50 5.8). The compounds were synthesized either by a simple microwave (MW)-promoted three-component reaction, or by a two-step one-pot procedure. For decoration of the oxindole ring system, rapid MW-assisted Suzuki-Miyaura cross-couplings (1 min) were performed. A small improvement of potency (pIC50 6.6 for the most potent compound) and an increased solubility could be achieved. As deduced from computational modelling and MD simulations it is proposed that the S-configuration of the spiro-oxindole dihydroquinazolinones accounts for the inhibition of IRAP.

An efficient one pot synthesis of 2-amino quinazolin-4(3H)-one derivative via MCR strategy

A novel multi-component reaction strategy was developed for the construction of important building blocks, 2-amino 3-substituted quinazolinone derivatives from isatoic anhydride and amine with electrophilic cyanating compound, N-cyano-4-methyl-N-phenylbenzenesulfonamide (NCTS). The quinazolinone synthesis proceeds via a sequential series of reactions such as nucleophilic attack of the amine group on the carbonyl group of isatoic anhydride followed ring opening and subsequent decarboxylation, nucleophilic attack of amine to nitrile, followed by heterocyclization.

A highly efficient method for the synthesis of novel 1'H-spiro[indene-2,2'-quinazoline]-1,3,4'(3'H)-trione derivatives

A series of novel ninhydrin-derived spiro-quinazolinone derivatives in moderate to good yields have been synthesised through a ferric chloride catalysed reaction in 1,2-dichloroethane.

Convenient and sequential one-pot route for synthesis of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives

A new and efficient synthetic process has been developed for preparation of 2-thioxoquinazolinone and quinazolinobenzothiazinedione derivatives. The related products were synthesized through reaction of isatoic anhydride, amines/anthranilic acids, and carbon disulfide (CS2) in the presence of potassium hydroxide in ethanol at reflux. Graphical abstract: [Figure not available: see fulltext.]

Reaction of isatoic anhydride, amine, and N,N′-dialkyl carbodiimides under solvent-free conditions: New and efficient synthesis of 3-alkyl-2-(alkylamino) quinazolin-4(3H)-ones

Heating a mixture of isatoic anhydride, amines, and N,N′-dialkyl carbodiimides under solvent-free conditions provided novel 3-alkyl-2- (alkylamino)quinazolin-4(3H)-one derivatives for the first time. The products were obtained in moderate to good yields without formation of any by-products. Copyright

Synthesis and in vitro study of platelet antiaggregant activity of some 4-quinazolinone derivatives

Some new 4-quinazolinones were prepared. Their antiplatelet activity was evaluated in vitro with respect to aggregation induced by ADP, collagen, arachidonic acid and the platelet serotonin release reaction. Most molecules showed an inhibiting power similar to that of acetylsalicylic acid under the same conditions, and even greater when aggregation was induced by ADP. Reduction of the 4-quinazolinone derivatives to their 1,2,3,4-tetrahydroquinazoline homologues produced an increase in platelet inhibitory action except when ADP is the inductor.